Or “How to show up more authentically with board members”

This past week, I was at a board retreat. Not facilitating a board retreat like I normally do. But attending the board retreat as a board member!

And my experience may help you with your nonprofit board members.

Begin With the End in Mind

As a certified FranklinCovey executive coach, I live by Covey’s Habit 2: Begin with the end in mind.

So as I prepared for this retreat, I knew I was investing 3 days away from my family and my work. So I wanted to make the most of this time. I’m also returning to this board after a few years away. I knew some of the participants but not all. And what I did know was likely old information.

As I looked at their LinkedIn profiles, I wondered if an AI deep research project might be more helpful.

Boy was it ever!

Here are the three steps I took.

Step 1: Asking AI to draft a prompt

I am fairly good at writing prompts. But I know the LLMs are much better. So I used this prompt in ChatGPT:

Could you help me draft a prompt for this research project?

Here’s the prompt I was thinking of: I’ll be attending the NSA (National Speakers Association) Foundation board retreat later this month.

We’ll be together for a couple days as guests of [host name]. Can you help me see what I can do to make the most of my time developing these relationships?

I’m interested in developing a new mastermind. And I’m interested in building out my Concord Leadership Group business and my EWTS Coaching company.

Could you research the LinkedIn profiles of all these people, and any credible outside information you can find that would help give me productive ways to connect with my colleagues that would be win-win?

Here are the LinkedIn profiles:

URL

URL

URL

ChatGPT created an amazing prompt starting with: “You are my relationship strategy + opportunity research assistant.” The rest of the prompt was much longer and more thorough than I would’ve come up with.

It was also not entirely accurate. So, like with all things Ai, I found editing the prompt made it better.

Step 2: Using the improved prompt

I then took the vastly improved prompt and entered it into ChatGPT, Claude, and Gemini. For each, I used the “deep research” mode.

I do this for three reasons:

Each has a different perspective and a different approach to doing research – the differences often keep me from missing opportunities.
Each model is being tweaked so I find the results to be inconsistent week-to-week. Using the different models helps me know which to focus on.
I am training the models. I’m not sure which one I’ll use most, so I attempt to give each helpful context about my work.

Each model had amazing insights. Connections I wasn’t aware of. New developments – books, projects, perspectives – I didn’t realize. And genuine areas of interest for me to ask them about.

Step 3: Figuring out how to bring the information to the retreat

The last part was challenging. Did I want to put the each note in the contact for each person in my phones contacts? Or in a comprehensive spreadsheet?

Each model shared the notes in different formats.

I ended up asking each model for a summary of their insights that I could paste into an Apple Note.

Why Apple Notes?

I wasn’t sure if I’d have my computer open and I find spreadsheets hard to read on my phone.
I thought switching between each individual contact during the retreat would be distracting.
And I knew Apple Notes would sync between my phone, iPad, and computer.

Apple Notes just work.

This experience blew my mind

I’ve worked with boards for over 30 years. Reported to board. Served on board. Coordinated with boards. Facilitated retreats and trainings for boards.

What blew my mind was how much I’ve squandered previous meetings!

In my previous board meetings, I’ve gone in knowing what I think I know about the others. My experiences. My notes. My conversations with members.

This project helped me to see what the board members were actually doing. Your mileage may vary with this but as these are all professional speakers, each had a digital footprint of their work and training frameworks. I was appallingly ignorant on most of them. I knew only surface amounts from brief social interactions.

During this retreat, rather than selfishly talk to them about my interests or goals, I was able to connect with them on theirs.

Better still, thanks to looking at the results in the multiple models prior to the retreat, I never had to consult my notes! I was able to be fully present. I was able to meet them as the person I really want to be – a good friend and colleague sincerely interested in them.

Now that the retreat is over, I am completely prepared for the follow up. The follow up actually started yesterday as we left. And was much more gratifying than I would’ve expected. I was truly building relationship, not extracting from people but working with them to create rich, fulfilling projects.

When was the last time you looked at your board members’ websites?

Familiarity can be misleading. When was the last time you found out what your board members do when they’re not at your nonprofit’s board meetings?

Over the years, I’ve been helped by Google Alerts. Google Alerts lets me know when my board members’ names showed up in a news story or blog. Great information that helped in building relationships.

But using tools like ChatGPT, Claude, and Gemini helped me understand more of the context these individuals lived in between meetings.

Try it this week

What ever tool you use, why not give it a try this week?

Ask the tool to help you draft a prompt for your goals. Tell it you’re interested in building relationships with the board members. And give it some insight into your professional goals.
Use that improved prompt in a deep research option of the tool or tools you prefer.
Identify insights that can help you have more authentic conversations at your next board meeting or dinner.

Not only will you have better insights to those who give of their time and talent to your nonprofit, you’ll also find yourself enjoying the unstructured communications more than you’d expect!